Adidas has parted ways with Kanye West, now known as Ye, over recent antisemitic remarks. The brand said it will cost it $246 million dollars this year as it loses out on highly lucrative Yeezy-branded products. West has been dropped by several other partners – including Gap – amid the backlash, dropping him from the Forbes billionaire ranks. He’s not the only celebrity to have a brand relationship go bust. Here are some costly breakups in this week’s Five for Friday.

#5: Paula Deen

Celebrity chefs have become huge brands themselves and are perfect for promoting food and kitchen gadgets. Paula Deen was a big name for the Food Network due to her Southern charm and penchant for butter-filled dishes. But in 2014, she admitted to using a certain racial slur in the past, which resulted in the loss of “Paula’s Home Cooking” and a deal with Smithfield Foods, costing her up to $5 million. Deen has since launched new TV programs and even sells jewelry on JTV.

#4: Allyson Felix and Simone Biles

Sometimes it goes the other way around with celebrities cutting ties with a brand. Seven-time Olympic gold medalist sprinter Allyson Felix backed out of renegotiating a deal with Nike. She says they tried to cut her pay by 70% while she was pregnant. In an op-ed for the New York Times, Felix wrote that she had asked the company to guarantee she wouldn’t be punished if she doesn’t perform at her best in the months surrounding childbirth. The company declined. Simone Biles, the most decorated gymnast ever, also parted ways with Nike, implying the company only cared about her achievements on the mat. Both superstars signed with Gap-owned Athleta, which they’ve said is more supportive of women.

#3: Madonna

Madonna was once the biggest pop idol on the planet. And in 1989, she signed a $5 million deal to star in a two-minute Pepsi commercial featuring her song, “Like a Prayer.” That would be more than $12 million today, according to the Bureau of Labor Statistics inflation calculator. Right after the commercial hit the airwaves, she released the actual music video for the song, which caught backlash for religious imagery including burning crosses. Pepsi decided to pull the ad and backed out of sponsoring her tour.

#2: Michael Vick

Michael Vick was electrifying as quarterback when he entered the NFL and his influence as both a runner and passer is still seen in the league today. But his involvement in a dogfighting ring stopped his career in its tracks. It also resulted in him serving nearly two years in prison. Vick lost out on $71 million that was left on his contract with the Atlanta Falcons and an estimated $50 million in endorsements. He made some of that back on his redemption tour upon release, signing a $100 million contract with the Philadelphia Eagles in 2011.

#1: Tiger Woods

Tiger Woods is still one of the highest-paid athletes in the world. He’s slated to make $65 million in endorsements alone in 2022. But after a scandal related to an extramarital affair in 2009, the golf great lost deals with AT&T, Accenture and Gillette, and with them, tens of millions of dollars. Nike stood by him, though, and in the end Tiger was able to secure numerous endorsement deals as he put that controversy behind him.